Hydrochloric Acid → HCID 20564928, compound

HRID 848818Notes

Reaction equation

HRID 848818 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([NH:14][C:15](N2CCCCC2)=[O:16])[N+:3]=1[O-:23].Cl.[OH-].[Na+].O1CC(=O)N=N1>>[NH2:1][C:2]1[N:3]2[O:23][C:15](=[O:16])[N:14]=[C:4]2[CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21866502OxadiazoloneHCID 178507850HCID 178507850, compound

Product 1

HCID 20564928HCID 20564928, compoundYield 73%

Procedure

2-Amino-4-(1-piperidinyl)-6-[(1-piperidinylcarbonyl)amino]pyridine 1-oxide (5.37 g., 0.017 mole) is dissolved in 100 ml. of 3N hydrochloric acid. After stirring the acid mixture for 0.5 hr. at room temperature, the mixture is cooled and neutralized with 50% sodium hydroxide affording a solid. The solid is collected, washed with water and air dried to provide 3.7 g. of crude oxadiazolone product, m.p. 283° C. (dec.). Further purification is carried out by dissolving the crude product in 300 ml. of methanol and treating the solution with activated charcoal. Concentration of the methanol solution to a volume of approximately 125 ml. and cooling affords 2.9 g. (73% yield) of 5-amino-7-(1-piperidinyl)-2H-[1,2,4]oxadiazolo[2,3-a]pyridin-2-one, m.p. 246.5° C. (dec.) (corr.).

Workup

  1. customThe solid is collected
  2. washwashed with water and air
  3. customdried
  4. customto provide 3.7 g
  5. customFurther purification
  6. dissolutionby dissolving the crude product in 300 ml
  7. additionof methanol and treating the solution with activated charcoal
  8. temperatureand cooling
  9. customaffords 2.9 g

Sources & evidence

ORD record
ord-4897e0a46261492da0e7f266c43c0f7c
Source dataset
uspto-grants-1981_10
Patent number
US04297498

Reaction notes

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